Synthesis of a Cholesteryl-HEG Phosphoramidite Derivative and Its Application to Lipid-conjugates of the Anti-HIV 5'TGGGAG3' Hotoda’s Sequence

doi:10.3390/molecules171012378

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Molecules 2012, 17(10), 12378-12392; doi:10.3390/molecules171012378

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Synthesis of a Cholesteryl-HEG Phosphoramidite Derivative and Its Application to Lipid-conjugates of the Anti-HIV ^5'TGGGAG^3' Hotoda’s Sequence

Domenica Musumeci and Daniela Montesarchio*

Dipartimento di Scienze Chimiche, Università di Napoli “Federico II”, Complesso Universitario di Monte Sant’Angelo, via Cintia 21, I-80126, Napoli, Italy

* Author to whom correspondence should be addressed.

Received: 19 September 2012; in revised form: 16 October 2012 / Accepted: 17 October 2012 / Published: 22 October 2012

(This article belongs to the Special Issue Nucleic Acid Analogs)

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Abstract: A novel phosphoramidite derivative of cholesterol, with an ether-linked hexaethylene glycol (HEG) spacer arm, has been obtained through simple and reproducible solid phase modified oligonucleotide synthesis manipulations. This building block and the known phosphoramidite derivative of 3b-(2-hydroxyethoxy)cholesterol have been exploited in standard oligonucleotide synthesis protocols for the preparation of 5'- conjugates of the G-quadruplex-forming ^5'TGGGAG³^' oligomer, known as the Hotoda’s sequence, to produce new potential anti-HIV agents.

Keywords: phosphoramidite; cholesterol; solid phase synthesis; anti-HIV G-rich oligonucleotides

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MDPI and ACS Style

Musumeci, D.; Montesarchio, D. Synthesis of a Cholesteryl-HEG Phosphoramidite Derivative and Its Application to Lipid-conjugates of the Anti-HIV ^5'TGGGAG^3' Hotoda’s Sequence. Molecules 2012, 17, 12378-12392.

AMA Style

Musumeci D, Montesarchio D. Synthesis of a Cholesteryl-HEG Phosphoramidite Derivative and Its Application to Lipid-conjugates of the Anti-HIV ^5'TGGGAG^3' Hotoda’s Sequence. Molecules. 2012; 17(10):12378-12392.

Chicago/Turabian Style

Musumeci, Domenica; Montesarchio, Daniela. 2012. "Synthesis of a Cholesteryl-HEG Phosphoramidite Derivative and Its Application to Lipid-conjugates of the Anti-HIV ^5'TGGGAG^3' Hotoda’s Sequence." Molecules 17, no. 10: 12378-12392.

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